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Chapter 11: Q32. (page 450)

Question: Enamines and imines are tautomers that contain N atoms. Draw a stepwise mechanism for the acid-catalyzed conversion of enamine X to imine Y.

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01

Step-by-Step SolutionsStep 1: Enamine and Imine

In enamine, there is a lone pair of nitrogen, and it’s bonded with an alkyl group. Imine has a carbon-nitrogen double bond. Imines are more stable than enamines.

02

Enamine hydrolysis

Enamine hydrolysis is the reverse of enamine formation. The lone pair of nitrogen drives the reaction, and a CN bond is formed with nitrogen carrying a positive charge.

The H-N conjugate base bond is cleaved, forming a carbon-nitrogen double bond.

Mechanism of acid-catalyzed conversion of enamine to imine

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